A series of 2,5-bis(diarylmethylene)-2,5-dihydrothiophenes and their furan, selenophene, and N-methylpyrrole analogs were synthesized in three steps either starting from 2,5-dilithiated five-membered heteroaromatics and 2 equiv of diaryl ketones or from 2,5-diaroyl five-membered heteroaromatics and 2 equiv of aryllithiums.